(<i>E</i>)-5-Benzyl-7-(3,4-dimethoxybenzylidene)-3-(3,4-dimethoxyphenyl)-2-phenyl-3,3a,4,5,6,7-hexahydro-2<i>H</i>-pyrazolo[4,3<i>c</i>] Pyridine
A new pyrazolo-pyridine analogue (title compound) was synthesized in two steps. The first stage was synthesis of monoketone curcumin analogue through Claisen–Schmidt reaction. The second stage was synthesis of the title compound through intermolecular cyclization under reflux condition. The structur...
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| Format: | Article |
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MDPI AG
2021-07-01
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| Series: | Molbank |
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| Online Access: | https://www.mdpi.com/1422-8599/2021/3/M1240 |
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| author | Enda Mora Adel Zamri Hilwan Y. Teruna Neni Frimayanti Ihsan Ikhtiarudin Noval Herfindo Elsa Natia Rindiana |
| author_facet | Enda Mora Adel Zamri Hilwan Y. Teruna Neni Frimayanti Ihsan Ikhtiarudin Noval Herfindo Elsa Natia Rindiana |
| author_sort | Enda Mora |
| collection | DOAJ |
| description | A new pyrazolo-pyridine analogue (title compound) was synthesized in two steps. The first stage was synthesis of monoketone curcumin analogue through Claisen–Schmidt reaction. The second stage was synthesis of the title compound through intermolecular cyclization under reflux condition. The structure of the title compound has been confirmed by spectroscopic analysis including UV, FT-IR, HRMS, 1D NMR (<sup>1</sup>H-NMR, <sup>13</sup>C-NMR, 1D-TOCSY), and 2D NMR (COSY, HSQC, HMBC). Based on the DPPH assay, the compound has moderate antioxidant activity, with an IC<sub>50</sub> value of 194.06 ± 7.88 µg/mL (0.337 mM). |
| first_indexed | 2024-03-10T07:24:15Z |
| format | Article |
| id | doaj.art-8116eb96effd4282a7ac3d4ef4b67699 |
| institution | Directory Open Access Journal |
| issn | 1422-8599 |
| language | English |
| last_indexed | 2024-03-10T07:24:15Z |
| publishDate | 2021-07-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molbank |
| spelling | doaj.art-8116eb96effd4282a7ac3d4ef4b676992023-11-22T14:22:19ZengMDPI AGMolbank1422-85992021-07-0120213M124010.3390/M1240(<i>E</i>)-5-Benzyl-7-(3,4-dimethoxybenzylidene)-3-(3,4-dimethoxyphenyl)-2-phenyl-3,3a,4,5,6,7-hexahydro-2<i>H</i>-pyrazolo[4,3<i>c</i>] PyridineEnda Mora0Adel Zamri1Hilwan Y. Teruna2Neni Frimayanti3Ihsan Ikhtiarudin4Noval Herfindo5Elsa Natia Rindiana6Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Riau, Jalan H.R. Subrantas KM. 12.5, Pekanbaru 28293, IndonesiaDepartment of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Riau, Jalan H.R. Subrantas KM. 12.5, Pekanbaru 28293, IndonesiaDepartment of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Riau, Jalan H.R. Subrantas KM. 12.5, Pekanbaru 28293, IndonesiaDepartment of Pharmacy, Sekolah Tinggi Ilmu Farmasi (STIFAR) Riau, Jalan Kamboja, Pekanbaru 28293, IndonesiaDepartment of Pharmacy, Sekolah Tinggi Ilmu Farmasi (STIFAR) Riau, Jalan Kamboja, Pekanbaru 28293, IndonesiaDepartment of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Riau, Jalan H.R. Subrantas KM. 12.5, Pekanbaru 28293, IndonesiaDepartment of Pharmacy, Sekolah Tinggi Ilmu Farmasi (STIFAR) Riau, Jalan Kamboja, Pekanbaru 28293, IndonesiaA new pyrazolo-pyridine analogue (title compound) was synthesized in two steps. The first stage was synthesis of monoketone curcumin analogue through Claisen–Schmidt reaction. The second stage was synthesis of the title compound through intermolecular cyclization under reflux condition. The structure of the title compound has been confirmed by spectroscopic analysis including UV, FT-IR, HRMS, 1D NMR (<sup>1</sup>H-NMR, <sup>13</sup>C-NMR, 1D-TOCSY), and 2D NMR (COSY, HSQC, HMBC). Based on the DPPH assay, the compound has moderate antioxidant activity, with an IC<sub>50</sub> value of 194.06 ± 7.88 µg/mL (0.337 mM).https://www.mdpi.com/1422-8599/2021/3/M1240monoketone curcumin analoguepyrazolo-pyridine analogueClaisen-Schmidt condensationintermolecular cyclizationDPPH assayantioxidant |
| spellingShingle | Enda Mora Adel Zamri Hilwan Y. Teruna Neni Frimayanti Ihsan Ikhtiarudin Noval Herfindo Elsa Natia Rindiana (<i>E</i>)-5-Benzyl-7-(3,4-dimethoxybenzylidene)-3-(3,4-dimethoxyphenyl)-2-phenyl-3,3a,4,5,6,7-hexahydro-2<i>H</i>-pyrazolo[4,3<i>c</i>] Pyridine Molbank monoketone curcumin analogue pyrazolo-pyridine analogue Claisen-Schmidt condensation intermolecular cyclization DPPH assay antioxidant |
| title | (<i>E</i>)-5-Benzyl-7-(3,4-dimethoxybenzylidene)-3-(3,4-dimethoxyphenyl)-2-phenyl-3,3a,4,5,6,7-hexahydro-2<i>H</i>-pyrazolo[4,3<i>c</i>] Pyridine |
| title_full | (<i>E</i>)-5-Benzyl-7-(3,4-dimethoxybenzylidene)-3-(3,4-dimethoxyphenyl)-2-phenyl-3,3a,4,5,6,7-hexahydro-2<i>H</i>-pyrazolo[4,3<i>c</i>] Pyridine |
| title_fullStr | (<i>E</i>)-5-Benzyl-7-(3,4-dimethoxybenzylidene)-3-(3,4-dimethoxyphenyl)-2-phenyl-3,3a,4,5,6,7-hexahydro-2<i>H</i>-pyrazolo[4,3<i>c</i>] Pyridine |
| title_full_unstemmed | (<i>E</i>)-5-Benzyl-7-(3,4-dimethoxybenzylidene)-3-(3,4-dimethoxyphenyl)-2-phenyl-3,3a,4,5,6,7-hexahydro-2<i>H</i>-pyrazolo[4,3<i>c</i>] Pyridine |
| title_short | (<i>E</i>)-5-Benzyl-7-(3,4-dimethoxybenzylidene)-3-(3,4-dimethoxyphenyl)-2-phenyl-3,3a,4,5,6,7-hexahydro-2<i>H</i>-pyrazolo[4,3<i>c</i>] Pyridine |
| title_sort | i e i 5 benzyl 7 3 4 dimethoxybenzylidene 3 3 4 dimethoxyphenyl 2 phenyl 3 3a 4 5 6 7 hexahydro 2 i h i pyrazolo 4 3 i c i pyridine |
| topic | monoketone curcumin analogue pyrazolo-pyridine analogue Claisen-Schmidt condensation intermolecular cyclization DPPH assay antioxidant |
| url | https://www.mdpi.com/1422-8599/2021/3/M1240 |
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